An aerial view of a town with a river, buildings, and surrounding greenery.

Apartments in Chestertown for Rent

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chestertown apartments

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
$136 nightly
The price is $150
Nov 16 - Nov 17
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.

2. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (35 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
$303 nightly
The price is $335
Nov 15 - Nov 16
Total with taxes and fees
Newly restored apartment in the heart of Chestertown
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

3. Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (33 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
$110 nightly
The price is $117
Nov 18 - Nov 19
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

4. Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (35 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
$256 nightly
The price is $283
Nov 14 - Nov 15
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A bathroom with two shelves; the top shelf holds two bottles of Eucalyptus Mint body wash and conditioner, and the bottom shelf holds a bar of Eucalyptus Mint body wash.

5. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
$176 nightly
The price is $191
Nov 23 - Nov 24
Total with taxes and fees
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

6. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
$189 nightly
The price is $206
Nov 23 - Nov 24
Total with taxes and fees
Beachcomber Suite
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

7. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
$130 nightly
The price is $138
Nov 16 - Nov 17
Total with taxes and fees
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Stylish kitchen with open layout and island seating

8. Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
Cape Saint Claire
10.0 out of 10, Exceptional, (9 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$405 nightly
The price is $461
Nov 14 - Nov 15
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes
A waterfront with docked boats, a water taxi, and historic buildings.

9. Cozy Fells Point Gem / In The Heart of Fells Point

Cozy Fells Point Gem / In The Heart of Fells Point
Fells Point
9.8 out of 10, Exceptional, (218 reviews)
"It’s a cozy, clean, and cute apartment. We enjoyed our stay very much and the location is wonderful…within walking distance of all the restaurants and attractions you could want."
United States
Carol
$186 nightly
The price is $215
Nov 17 - Nov 18
Total with taxes and fees
Cozy Fells Point Gem / In The Heart of Fells Point
A bed with a dark headboard, a mirror, a potted plant, and a snack basket on the bedside table.

10. Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals

Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
Nottingham City
10.0 out of 10, Exceptional, (1 review)
"At the end of a multi-city trip filled with mixed hotel experiences, this stay was a true breath of fresh air. Everything was spotlessly clean, beautifully organized, and exactly as pictured. What truly set it apart were the thoughtful touches throughout the space—it was clear our host anticipated our every need, which even saved us an extra trip to the store! Parking was effortless, and the location made getting into the city by car or public transit super easy. Communication with our host was...
United States
Jennifer R.
$223 nightly
The price is $257
Nov 16 - Nov 17
Total with taxes and fees
Private Suite: Hotel Perks, Snacks & Fast WiFi near Baltimore & Top Hospitals
A modern living room with a sofa, a television mounted on the wall, and a fireplace.

11. Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk

Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk
Berea
$260 nightly
The price is $300
Nov 23 - Nov 24
Total with taxes and fees
Crown Suite Slps 7 2 Full BR Wd Floor Free ST Prk
A spacious hallway with a staircase, a seating area with a sofa and armchairs, and a large window with a stained glass design.

12. Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC

Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
Greektown
9.8 out of 10, Exceptional, (18 reviews)
"Perfect Maryland trip"
United States
Rosa E.
$206 nightly
The price is $238
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Baltimore with WiFi, AC
A kitchen with a wooden countertop, a stove, and a refrigerator.

13. 18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.2 out of 10, Wonderful, (16 reviews)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
$354 nightly
The price is $404
Nov 14 - Nov 15
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"Reasonable price. Clean place"
Arthur 1-night trip
Posted 12 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Find out more about Chestertown

Chestertown Apartments information

Number of reviews
445
Accommodation
74 Apartments
Lowest Price
$138
Highest Price
$461

Frequently asked questions

What's it like to stay at an apartment in Chestertown?
You can choose from 5 apartments in Chestertown for your vacation.
Why should you consider apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for my stay in Chestertown?
Here are some of the more popular apartments in the area to choose from: First Floor Studio Apartment in Historic Chestertown: Includes a private pool, free WiFi, and private patios. A fitness center and onsite laundry facilities are on site. WORLD'S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD: Located 16.1 mi/25.9 km away in Earleville. Free WiFi and Smart TVs are included. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL: Located in Aberdeen, 18.4 mi/29.5 km away. Includes free WiFi, private patios, and Smart TVs. Onsite laundry facilities and a hot tub are on site. Cozy Fells Point Gem / In The Heart of Fells Point: It's located in Baltimore, 28.3 mi/45.5 km from Chestertown. Includes free WiFi and Smart TVs.
How many apartments can I expect to find in Chestertown?
Expedia has 5 apartments to book in Chestertown.
What can I expect from the weather during my trip to Chestertown?
Weather is only one factor, but it can really affect your travel plans, especially when you're planning an extended stay in Chestertown. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What should I see and do in Chestertown?
Cultural attractions include Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater, whereas Northern Chesapeake Bay and Chesapeake Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Chestertown Historic District and Rolphs Wharf Marina.
What's the best way to get to and around Chestertown?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, consider renting a car to take in more sights.

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